Questions tagged [inductive-effect]

Use for questions regarding the so called inductive effect of substituents on properties of compounds.

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Why is ethanol more acidic than acetone?

The acidity of a compound is determined by the stability of its conjugate base and the major structure of enolate has a negative charge on the Oxygen atom. Moreover, the negative charge on the O-atom ...
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Effect of distance on the mesomeric effect

I have always thought that mesomeric effect is somewhat dependent on distance. But I recently came across a question where I was asked to predict the order of stability of o-methoxyphenyl carbocation ...
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Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?

If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows: Even after deprotonation, it has intramolecular hydrogen bonding as follows: My question: p-...
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Stability of meta ethyl and meta methyl benzene carbocations respectively

It is known that Methyl has a greater +I effect than Ethyl, but here, in this case, the condition is satisfied in the para benzene carbocations whereas, in the meta forms, it is the opposite. Shouldn'...
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Basic character of amines in rings [duplicate]

Why does the size of the ring affect the basicity of amines? What is the factor deciding the basicity in this case? I've read about the s-character increase concept but didn't quite understand it.
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Carbocation formation and stability from bromo compounds

When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised. This is my ...
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37 views

Comparing nucleophilic strengths of tetrahydropyran and (2R,6R)-2,6 dimethyltetrahydropyran

Compare the nucleophilic strengths of the following two compounds: According to me it should be the second one, that is, (2R,6R)-2,6-dimethyltetrahydropyran because the methyl groups would exert +I ...
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210 views

How do steric effects affect inductive effect in compounds with tetravalent nitrogen?

I want to compare the electron density on methyl group between tri‐tert‐butyl(methyl)azanium (1) and triisopropyl(methyl)azanium (2), i.e. essentially the inductive effects of $\ce{-\overset{+}{N}R3}$ ...
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Evaluating inductive effects in cyclic compounds

I was required to find the products on heating the hydroxide of; Now it's easy enough to find the answer; Hoffman elimination isn't going to happen from the methyl, and the n-propyl doesn't have $\...
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58 views

Acidic nature comparison; benzoic acid and phenylacetic acid

The $\ce{pK_a}$ values of benzoic acid and phenylacetic acid are around 4.2 and 4.31 respectively. In benzoic acid, you have the resonance being the dominating effect, destabilizing a conjugate base ...
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What does acidity of para-alkyl substituted phenols depend on?

Problem Arrange the following organic compounds in decreasing order of acidity. Answer Question According to my knowledge the answer should be P, Q, R, S. As we proceed from P to S we are ...
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127 views

Stabilization of multiple bonds through inductive effects

In the conversion of m-chloroanisole to m-anisidine using $\ce{NaNH2}$ and liquid $\ce{NH3}$, apparently the reason the $\ce{NH2-}$ goes for the meta- position instead of the para position is that, in ...
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Why does the carboxylate ion show positive inductive effect?

While solving some problems on general organic chemistry, I came across this question that asked for the nature of inductive effects of $\ce{-CH_3}, \ce{-CO_2^-}, \ce{-Br}, \ce{-NH_3^+}$. And in the ...
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Confusion in comparing the contribution of resonating structures to resonance hybrid [closed]

So I was comparing the $+M$ effect of $\ce{-CH^-_2}$, $\ce{-NH^-}$ and $\ce{-O^-}$. Answer was given as: $$ \ce{-CH^-2 > -NH^- > -O^-}$$ So, I attach them with ethene and made their respective ...
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Relative acidity of acetic acid derivatives with strongly withdrawing substituents

What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following: $\ce{O2N-CH2-CO2H},$ $\ce{Me3\overset{+}{N}-CH2-CO2H},$ $\ce{NC-CH2-CO2H},$ $\ce{HO-CH2-CO2H}?$ Since only the groups ...
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Combined Effect of Steric Inhibition of Resonance and Inductive Effect

While qualitatively comparing the acidic nature of o-methyl benzoic acid and benzoic acid, we consider the steric effect due to which the $\ce{-COOH}$ group loses its planarity and the +M effect of $\...
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80 views

How to explain regioselectivity in nucleophilic aromatic substitution

I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide: I have predicted that the para-substituted product is formed as ...
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Order of −I effect among ethenyl and 1-propenyl groups

We know that both ethenyl $\ce{-CH=CH}_2$ and 1-propenyl $\ce{-CH=CH-CH3}$ are electron-withdrawing groups when attached to hydrocarbon chain. Which one has greater electron withdrawing power? The $\...
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Inductive effect vs electronegativity [closed]

Why is the inductive effect of chlorine, bromine, and iodine stronger than that of hydroxy group, even though oxygen is more electronegative?
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195 views

Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?

I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
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244 views

Estimation of dipole moments in aromatic compounds

If it asks to compare dipole moment in aromatic compounds then do we see inductive or resonance effects or do we see a mix of both? E.g. we have to compare dipole moment in pyrrole and furan then in ...
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477 views

Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction

Beginning with a reference to a well known question. Order by reactivity towards SN1 reaction. According to some facts about SN1 reactions, rate depends on: Stability of carbocations Better leaving ...
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Inductive effect of acetyl group

Question: Since the acetyl group provides $-M$, methyl $+I$ and chlorine $-I$, it is obvious that the correct order is as given in option $(a)$ However while solving such questions I would compare ...
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Does the electron displacement effect act only on sigma electrons?

Our teacher told us that the inductive effect or the electron displacement effect can only affect the sigma electrons. I did not understand why this should be. I reasoned it can not affect the pi ...
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378 views

Carbanion Stability order [duplicate]

Why is a 3° Carbanion unstable than 1° Carbanion? Carbon atom with negative charge will become little electropositive relative to a neutral carbon. So if a Carbanion is attached to three neutral ...
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243 views

The most acidic hydrogen among ethane, ethene, ethyne and allene

Among $$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$ I need to find out the one having highest acidic hydrogen. As per my observations, there are two equivalent resonating ...
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Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?

Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
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Does Cl- Have more -I effect or +M effect ( Resonance effect)?

In this question my answer was (A) because i though $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$ . But the correct answer is (D) and my teacher's reason is that chlorine has more ...
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Inductive effect of -NHMe

Why does $\ce{-NHMe}$ show -I effect. I think it should be opposite. I know that $\ce{-Me}$ groups are electron donating in nature. So the nitrogen atom will have a small $\delta^-$ charge. So then ...
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Methyl group and acidic nature [duplicate]

After reading various answers here on StackExchange (like Why is the methyl group electron-donating via the inductive effect? and Strongest negative inductive effect group between trimethylammonium, ...
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613 views

Why is formic acid stronger than acetic acid [duplicate]

Even when acetate ion is stabilized due to resonance why is it a weaker acid than formic acid. It is true that acetic acid has +I effect due to methyl group present on it but resonance is a stronger ...
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Problem in defining the Inductive effect

Inductive effect is introduced in many textbooks by giving an example of an alkyl halide $R-X$. The bond C1-X is polar due to electronegativity difference, therefore X gains partial negative charge ∆(-...
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270 views

Stability of carbocation directly attached to a halogen atom [duplicate]

I have two compounds.. How is the first one more stable? As I have been taught that -I effect of Chlorine dominates its +R effect but to explain this case, My teacher is saying that because of the ...
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Para effects on substituents in aromatic compounds

I wanted to know how to compare the following compounds on basis of acidic strength. I have to find the acidic strength of following compounds with $\mathrm{X}=\ce{CH3, \ OCH3,}$ and $\ce{NO2}$. For ...
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Comparison of basicity of Aniline, p-Anisidine, and o-Anisidine [duplicate]

I have a question where I am required to compare the basicity of Aniline, o-Anisidine, and p-Anisidine. Now here's what I do know:- In ortho substituted aniline, an ortho effect acts which reduces ...
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Comparison between groups with -I effects

So I have a few questions in my book that require me to compare between two different groups on the basis of their -I effects. I have a few questions on this that have been bugging me for quite a ...
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Effect of phenyl and vinyl substituents on Acidity of carboxylic

Recently I came across this statement in my textbook: Direct attachment of groups such as phenyl or vinyl to the carboxylic acid, increases the acidity of corresponding carboxylic acid contrary ...
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Odd looking carbocation stability order [duplicate]

I am studying introductory organic chemistry, suddenly this one started looking odd, The carbocation stability for three compounds as given by my book is shown below, Let me call those as ...
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Change in inductive effect of a susbstituent when -R group replaces -H atom

There are several examples where the negative inductive effect of a substituent gets increased when a hydrogen atom on that substituent is replaced by an alkyl group. Some particular examples: $$\ce{...
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Why O and N promote SN1 but C=O inhibit SN1 although both are electron-withdrawing?

Source: Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry 2th Edition, 339. The general idea I got so far, is that, carbocation will be more stable if the + charge at central C is ...
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How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?

I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
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What is the stability order of the carbocation and carboanion?

So I came up with examples as below: 1 2 Now I am confused about the +I and -I effect in these structures since to my knowledge it can only be applied when there is a substituent (I might be wrong)...
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Which substitutent should be placed on axial position in SCl2(OCH3)2?

According to Bent's rule, in $\mathrm{sp^3d}$ more electronegative element is placed on the axial position, so between $\ce{Cl}$ and $\ce{OCH3}$ in $\ce{SCl2(OCH3)2}$ which should be placed on axial ...
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Does an electronegative atom which carries a negative formal charge withdraw electrons by induction?

Electronegative atoms withdraw electrons by their inductuve effect. Does this fact remain true even when they are heavily loaded with electrons through negative formal charge? Are these two ideas ...
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Inductive effect of alkyl ammonium groups

Why $\ce{-NR3+}$ has more -I effect than $\ce{-NH3+}?$ And what about order of $\ce{-NHR2+}$ and $\ce{-NH2R+}?$ My attempts I got idea about electronegativity of carbon atom in $\ce{R}$ is more than ...
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Which of the following groups show +M and -I effect?

Which of the following group show +M and -I effect? (A) $\ce{-\underset{\underset{\huge O}{||}}{C}-F}$ (B) $\ce{-\underset{\underset{\huge O}{||}}{C}-OR}$ (C) $\ce{-O^-}$ (D) $\ce{-OH}$ Answer is ...
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When 2-pentene reacts with HBr, what will be the major product?

If we consider the first step (formation of carbocation by the attack of the proton). A couple of textbooks I referred say that when the substituents on the $\ce{C=C}$ are different, the direction of ...
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171 views

Confusions about inductive effect and acid strength

If one of the hydrogens in the alkyl side chain of ethanoic acid is replaced with an atom of Chlorine, the acid has a larger Ka value. My book says this is since the Cl "borrows" electron density from ...
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254 views

Which of the two structures is more stable?

Which of the two structures is more stable? As far as I know, alkenes with a greater number of hyperconjugating structures are more stable. Hyperconjugation has a greater stabilizing effect than ...
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Does hyperconjugation into sigma-star explain methylamine's increased basicity relative to ammonia?

The inductive effect with the polarisation of the C-N bond obviously plays a role in stabilising the positive charge of the conjugate acid. But given the similar electronegativities for C and H, CH3 ...